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    City: Chestertown, MD
    Listing Status: Active
    Map
    115 Properties Available In Chestertown

    115 Properties Available In Chestertown

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    • Price-High To Low
    • Price-Low To High
    • Newest Listings
    • Beds (Most)
    • Baths (Most)
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    MD >Chestertown >
    Market Insights
    21324 PERSIMMON DR, Chestertown, MD 21620
    1/13
    Open Sat 11AM-1PM
    3D

    $199,000

    2 Beds1 Bath1,232 SqFt

    21324 PERSIMMON DR, Chestertown, MD 21620

    MLS# MDKE2006816

    Listed by Benson & Mangold, LLC

    Bright MLS (BMLS)
    10720 FORESTON RD, Chestertown, MD 21620
    1/42
    Open Sat 11AM-1PM

    $335,000

    3 Beds2 Baths1,412 SqFt

    10720 FORESTON RD, Chestertown, MD 21620

    MLS# MDKE2006800

    Listed by Compass

    Bright MLS (BMLS)
    106 QUEEN ST S, Chestertown, MD 21620
    1/92
    Open Sat 10AM-12PM

    $829,000

    3 Beds4 Baths2,472 SqFt

    106 QUEEN ST S, Chestertown, MD 21620

    MLS# MDKE2006152

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    210 N QUEEN ST, Chestertown, MD 21620
    1/36
    New

    $735,000

    4 Beds3 Baths2,730 SqFt

    210 N QUEEN ST, Chestertown, MD 21620

    MLS# MDKE2006744

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    109 CEDAR ST, Chestertown, MD 21620
    1/22
    New

    $325,000

    3 Beds3 Baths1,397 SqFt

    109 CEDAR ST, Chestertown, MD 21620

    MLS# MDKE2006792

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    200 MANOR AVE, Chestertown, MD 21620
    1/34
    New

    $325,000

    4 Beds2 Baths2,198 SqFt

    200 MANOR AVE, Chestertown, MD 21620

    MLS# MDKE2006808

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    121 METCALF RD, Chestertown, MD 21620
    1/10
    New

    $264,900

    3 Beds2 Baths3,920 Sqft Lot

    121 METCALF RD, Chestertown, MD 21620

    MLS# MDKE2006678

    Listed by Real Broker, LLC - Chester

    Bright MLS (BMLS)
    409 CALVERT ST, Chestertown, MD 21620
    1/9
    Active

    $155,000

    3 Beds2 Baths1,192 SqFt

    409 CALVERT ST, Chestertown, MD 21620

    MLS# MDKE2006794

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    7680 COUNTRY CLUB LN, Chestertown, MD 21620
    1/43
    Active

    $885,000

    5 Beds4 Baths2,639 SqFt

    7680 COUNTRY CLUB LN, Chestertown, MD 21620

    MLS# MDKE2006758

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
    9126 FAIRLEE RD, Chestertown, MD 21620
    1/20
    Active

    $344,000

    3 Beds2 Baths1,216 SqFt

    9126 FAIRLEE RD, Chestertown, MD 21620

    MLS# MDKE2006764

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    896 WASHINGTON AVE, Chestertown, MD 21620
    1/34
    Active

    $325,000

    3 Beds1 Bath1,000 SqFt

    896 WASHINGTON AVE, Chestertown, MD 21620

    MLS# MDKE2006750

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    25750 COLLINS AVE, Chestertown, MD 21620
    1/50
    Active

    $468,000

    3 Beds2 Baths3,262 SqFt

    25750 COLLINS AVE, Chestertown, MD 21620

    MLS# MDKE2006546

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    101 S MILL ST, Chestertown, MD 21620
    1/39
    Active

    $515,000

    2 Beds3 Baths1,476 SqFt

    101 S MILL ST, Chestertown, MD 21620

    MLS# MDKE2006674

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    517 ROUND TOP RD, Chestertown, MD 21620
    1/28
    Price Dropped by $25K

    $299,900

    3 Beds1 Bath1,248 SqFt

    517 ROUND TOP RD, Chestertown, MD 21620

    MLS# MDQA2017680

    Listed by Keller Williams Flagship

    Bright MLS (BMLS)
    104 CONLEY DR, Chestertown, MD 21620
    1/27
    Price Dropped by $7K

    $239,900

    3 Beds2 Baths1,280 SqFt

    104 CONLEY DR, Chestertown, MD 21620

    MLS# MDKE2006686

    Listed by Cummings & Co. Realtors

    Bright MLS (BMLS)
    104 ACORN DR, Chestertown, MD 21620
    1/26
    Price Dropped by $9K

    $275,000

    3 Beds3 Baths1,900 SqFt

    104 ACORN DR, Chestertown, MD 21620

    MLS# MDKE2006668

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
    234 N COLLEGE AVE, Chestertown, MD 21620
    1/3
    Price Dropped by $10K

    $90,000

    2 Beds1 Bath1,296 SqFt

    234 N COLLEGE AVE, Chestertown, MD 21620

    MLS# MDKE2006670

    Listed by Cummings & Co Realtors

    Bright MLS (BMLS)
    8796 MARYLAND PKWY, Chestertown, MD 21620
    1/60
    Active

    $1,650,000

    9 Beds7 Baths4,776 SqFt

    8796 MARYLAND PKWY, Chestertown, MD 21620

    MLS# MDKE2006596

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    110 PROSPECT ST, Chestertown, MD 21620
    1/6
    Price Dropped by $5K

    $74,900

    3 Beds2 Baths2,210 SqFt

    110 PROSPECT ST, Chestertown, MD 21620

    MLS# MDKE2006626

    Listed by ANR Realty, LLC

    Bright MLS (BMLS)
    1904 PONDTOWN RD, Chestertown, MD 21620
    1/11
    Active

    $265,000

    3 Beds1 Bath1,967 SqFt

    1904 PONDTOWN RD, Chestertown, MD 21620

    MLS# MDQA2017480

    Listed by Keller Williams Flagship

    Bright MLS (BMLS)
    10781 FERMOY RD, Chestertown, MD 21620
    1/54
    Price Dropped by $20K

    $429,900

    4 Beds3 Baths2,160 SqFt

    10781 FERMOY RD, Chestertown, MD 21620

    MLS# MDKE2006640

    Listed by Real Broker, LLC - Chester

    Bright MLS (BMLS)
    213 BYFORD DR, Chestertown, MD 21620
    1/39
    Active

    $380,000

    4 Beds2 Baths1,277 SqFt

    213 BYFORD DR, Chestertown, MD 21620

    MLS# MDKE2006026

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    21172 WYOMING AVE, Chestertown, MD 21620
    Active

    $200,000

    4 Beds1 Bath2,920 SqFt

    21172 WYOMING AVE, Chestertown, MD 21620

    MLS# MDKE2006642

    Listed by Blue Star Real Estate, LLC

    Bright MLS (BMLS)
    22470 FAIRGALE FARM LN, Chestertown, MD 21620
    1/52
    Active

    $1,450,000

    4 Beds5 Baths4,257 SqFt

    22470 FAIRGALE FARM LN, Chestertown, MD 21620

    MLS# MDKE2006502

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
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    Bayside Realty
    Dale Hunter Jr
    +1(443) 829-5828
    dalehunterjr@baysiderealtymd.com
    23458 Scotts Ln, St Michaels, MD 21663, USA
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        Market Snapshot
    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

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    Bayside Realty
    Dale Hunter Jr
    +1(443) 829-5828
    dalehunterjr@baysiderealtymd.com
    23458 Scotts Ln, St Michaels, MD 21663, USA
        Home
        Buy
        1. All Listings
        2. Featured Listings
        Sell
        1. Sell My Home
        2. Home Valuation
        3. Recent Sold
        Rent
        1. Rental Listings
        Featured Areas
        1. Easton Overview
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        4. Chestertown Overview
        5. Saint Michaels Overview
        6. Ridgely Overview
        7. Berlin Overview
        About
        1. My Team
        2. About Us
        3. Contact Us
        4. Reviews
        Market Snapshot
    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

    Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility